Learning and Sharing at #digitalwomenleaders

I would have never done this on my own, but with some healthy encouragement from my colleagues and teammates, I helped WordPress.com VIP sponsor the ONA-Poynter Leadership Academy for Women in Digital Media.

The attendees were impressive. We were one of three sponsors (along with Google and Ford Foundation) for this workshop of women in leadership positions at media companies. 400+ women applied for 28 spots. There were also around 10-15 faculty, all female leaders from various media companies.

The curriculum was top-notch. Every attendee had to complete a 360 Review (gather feedback from their lead, the team they lead, and others), and a Myers-Briggs test before coming to the workshop. With this detailed feedback, the trainers broke the cohort up into groups depending on the type of lead and personality they were, and then gave them specific coaching techniques. Every coach had a wealth of information on their coachees. Considering that the workshop is free for attendees, I was amazed by how specific and tailored the curriculum was.


The women came prepared to share. While there were lots of faculty, the learning came from the attendees speaking up, listening, and building upon shared experiences. This type of honesty could only happen in an open and supportive environment, and with the proper cues and questions, which the ONA-Poynter faculty worked hard to create.

As part of the sponsorship, I had to speak. This part gave me a lot of pause, because as a female team lead I wanted to share a bit of my story, but I hadn’t really done that before. I almost didn’t go through with it, but after meeting the attendees and hearing some of their stories, I decided to share mine.

I ended up breaking up my presentation into two parts. First, a quick demo about All Things WordPress + Media. This part I do all the time. Second, a few words about why I was there.

This is what I chose to share. Back in February, the VIP Support team had a long conversation at our meetup in Barcelona about diversity. Diversity (in every way) was important to our team and we wanted to make efforts to improve that, which is why we were helping sponsor this event. Of the 30+ people on Team VIP, only three are women. My team primarily works with leaders in digital media (CTOs, VPs, Directors of Tech, Lead Devs), and less than 10 percent of our clients are women. I regularly host BigWP events all around the world, and in 3 years, we’ve only had a handful of female speakers.

I also I spoke about becoming a female team lead, and how weird that was when almost everyone I worked with internally and externally was male. I shared that it takes extra courage to speak up when you’re the only woman in a room full of men, courage I often did not have. I also shared that, when you’re surrounded by colleagues and clients not like you, you spend a lot of time trying to be like everyone else. It was a long and frustrating road for me to stop mimicking other people, and start validating the things I was good at.

When I became a lead in 2014, there were very few female leads at Automattic, and the imposter syndrome was paralyzing. I read out loud the phrases that would repeat through my head on a daily basis: I am not smart enough. I am not old enough. I am not technical enough. I am not forceful enough. I am not experienced enough. I don’t work hard enough. 

Reciting these phrases was hard for me. But I think the attendees felt what I felt. After I shared my story, attendees came up to me to give me hugs, and to say thank you.

Photo courtesy of Poynter/ONA.

Which brings me back to the Academy’s support network. I didn’t have one, but had to work to create one over the last two years – and it has really helped me. The women who were a part of the 2016 cohort now have a built-in network, and will keep in touch via Facebook group. The members of the 2015 cohort say they still use their Facebook group almost every single day, to ask questions, get help, bounce ideas. Many of them have accelerated at their existing job, or were recruited for new jobs. What an incredible program to be a part of, and I’m so proud we were there to help sponsor it.

Even though I could only attend for two days of the weeklong training, it was definitely a highlight of my year. By sharing their stories with me, the attendees and faculty gave me inspiration, courage, and support. I’m happy I decided to share my story as well.

More reading: